Ethanol → 3-Methylthio-4-chromanone

Participants

Reaction Steps

After 10.4 g of 3-bromo-4-chromanone [synthesized in accordance with procedures described in W. S. Johnson, et al., J. Am. Chem. Soc., vol.66, p.218 to 220 (1944)] was dissolved into 42 ml of ethanol, 21.3 ml of a 15% aqueous solution of a sodium salt of methylmercaptan was added dropwise thereto. After the stirring for 2 hours at room temperature, the reaction mixture was poured into 300 ml of cold water. An organic layer was extracted with 200 ml of ether, and the ether layer was sequentially washed with a sodium chloride aqueous solution and water. After the ether layer was dried with magnesium sulfate, the solvent was removed by evaporated under vacuum. The residue was isolated and purified through a silica gel column (elute: hexane/ethyl acetate=3/1) to provide 1.52 g of 3-methylthio-4-chromanone (yield: 17%).

Provenance & Evidence